Viscous fat compositions having low amounts of trans-fat, methods and products

ABSTRACT

Fat-containing compositions comprise a fat component having less than 40% by weight of trans fat and a cyclodextrin, wherein at least about 25% of the cyclodextrin in the composition is bound to the fat. The fat compositions as provided herein can be substantially more viscous or harder than a like fat composition that does not contain cyclodextrin that is bound to the fat. Food products and methods of use of food products are described.

CROSS-REFERENCE TO RELATED APPLICATIONS

This present application represents a divisional application of U.S.patent application Ser. No. 11/158,747, filed Jun. 22, 2005, whichclaims the benefit of U.S. Provisional Application No. 60/581,993, filedJun. 22, 2004, which is hereby incorporated by reference.

FIELD OF THE INVENTION

The invention relates to fat-containing compositions. More specifically,the invention relates to viscous fat-containing compositions having lowamounts of trans-fat and to methods of binding cyclodextrin to fats.

BACKGROUND

Recent studies have suggested that trans fatty acids in food productsand food intermediates can be detrimental to the general health and wellbeing of consumers in that it contributes to obesity and other healthrelated issues.

Trans fatty acids are unsaturated fatty acids in which the hydrogens ofa double bond (or unsaturation) are on opposite sides of the molecule.The trans isomer of the fatty acid causes the carbon chain to assume astraight-chain configuration similar to that of a saturated fat. Transfatty acids are primarily formed through the metal-catalyzed process ofhydrogenation, however they have also been found to form naturally atlow levels in cow's milk. By hydrogenating oils through industrialprocessing, hydrogen atoms are added to unsaturated sites on fattyacids, creating a larger population of saturated fats in the oil. In apartially-hydrogenated oil, some of the unsaturated fatty acids remain.However, the processing causes some of the double-bonds of theunsaturated fatty acids to undergo isomerization to the transconfiguration.

Partial hydrogenation of fats was introduced into the U.S. food supplybeginning in 1910. The practice was put into widespread use in the1940's in order to make semisolid fat products. The process ofhydrogenation raises the melting point of a fat and increases the solidfat content. The stability of the fat is greatly enhanced throughhydrogenation by reducing susceptibility to oxidation and subsequentrancidity. Therefore, positive contributions to shelf-life, texture andtaste of food products are imparted by hydrogenated and partiallyhydrogenated fats.

Some scientific evidence shows that the trans fat that results frompartial hydrogenation of oils raises the total cholesterol in humans toa greater extent than saturated fats. Trans fat is known to increaseblood levels of low density lipoprotein (LDL), so-called “bad”cholesterol, while lowering levels of high density lipoprotein (HDL),known as “good” cholesterol.

Cyclodextrins have been used principally for the encapsulation ofinsoluble compounds on a molecular basis in order to enhance stability,reduce volatility and alter solubility as well as to increase shelf lifeof certain products. Such prior uses of cyclodextrins have been limitedto flavor carriers and protection of sensitive substances againstthermal decomposition, oxidation and degradation. In addition, morerecently, cyclodextrins have also been used to remove fatty acids andcholesterol from animal fats and to remove cholesterol and cholesterolesters from egg yolks.

One potential solution to the high cholesterol problem teaches thetreatment of the foodstuffs themselves with cyclodextrins rather thantreatment of the consumer. U.S. Pat. Nos. 5,498,437; 5,342,633 and5,063,077 discuss various processes for the removal of cholesterol andcholesterol esters from egg yolks, meat, animal fats, etc. It is thoughtthat by reducing the level of cholesterol in such foodstuffs thatoverall levels of cholesterol can be reduced in consumers. However,processing steps to such foodstuffs increases the cost of deliveringsuch products to market.

In some instances, a thickened fat is desired to provide dimensionalstability (e.g., to minimize fluid flow or keep a fat ingredient in aparticular location in a food article). At present, only threetechniques for providing a thickened fat such as for use in a foodproduct are practical. The first, hydrogenation, as described above,while useful and widely practiced undesirably results in the generationof trans fatty acids. The second technique involves addition of silicondioxide to an oil. For example, U.S. Pat. No. 3,669,681 describespreparing a shortening for products which are heated prior toconsumption, wherein edible oils are mixed with silicon dioxide and abridging compound with the result being a shortening that is asserted tonot weep or run at elevated temperatures while retaining desirable mouthfeel characteristics of the untreated oil.

While useful, current food regulatory restrictions restrict employmentof this technique. The third technique involves addition of sufficientamounts of hardstock, whether naturally occurring (such as palm oilhardstock) or synthetic (such as produced by hydrogenation), to an oilto provide desired amounts of thickening or hardening. Again, whileuseful, current consumer heath sensitivities favor minimization ofconsumption of such hardstock ingredients.

SUMMARY OF THE INVENTION

The present invention provides a new technique for thickening orhardening fats and oils that is both useful and commercially practical(i.e., both economically and from a commercial production standpoint).The present new fat thickening technique is inexpensive, simple tocommercially practice, and minimizes consumption of undesirable foodingredients such as trans fatty acids.

It has surprisingly been found that by binding cyclodextrin to fat inhigh binding ratios, a low trans fat content fat can be prepared havinga high viscosity. The resulting thickened fat has a low amount of freecyclodextrin. Thus, embodiments of the invention can leave little or noresidue on heating. Additionally, embodiments of the invention canabsorb little or no flavors other than from the food. Additionally, theresulting fat composition can exhibit enhanced resistance to oxidationof the fat, thereby prolonging useful storage life of the fatcomposition or food products containing the composition with diminishedobservance of rancidity of the fat. A fat-containing composition isprovided comprising a fat component having less than 40% by weight oftrans fat and a cyclodextrin, wherein at least about 25% of thecyclodextrin in the composition is bound to the fat. In additionalembodiments, the fat component has less than 20%, 10% or 2% of transfat. Alternatively, the fat component can be substantially free of transfat. In an embodiment of the present invention, the compositioncomprises less than about 50% saturated fat based on total fat content.In additional embodiments, the fat component has less than 25% or 15% ofsaturated fat based on total fat content. The fat compositions asprovided herein can be substantially more viscous (when a liquid), orharder (when a solid) than a like fat composition that does not containcyclodextrin that is bound to the fat. This thickening and/or hardeningof the fat can provide compositions that achieve desired physicalproperties even with little or no saturated fats. Thus, in oneembodiment the present invention can provide food products havingdesired organoleptic properties while achieving at least a 25% reductionin fat as compared to an appropriate reference food as described in 21CFR Sec 101.13(j)(1). Thickened fats are important for use in foodproducts in that they provide the required consistency at the correcttemperature to enable preparation of the food product. For example, afat having the consistency of shortening is required to make laminateddough products and certain baked goods. Without the relatively hardconsistency, the products would not have the texture that consumers havecome to expect. Additionally, the perceived melting point of the fatcontributes to the mouthfeel of the food product. The present inventionadvantageously provides the desired physical and general organolepticproperties of a thicker or harder fat without introduction oftrans-fats, thereby providing substantial healthful benefits.

Alternatively, bound fat/cyclodextrin compositions as provided hereincan be blended with saturated fats to achieve desired organoleptic andperformance properties with a substantial reduction in saturated fatcontent as compared to other food products that do not contain the boundfat/cyclodextrin compositions.

In another aspect of the present invention, food products are providedcomprising fat-containing compositions comprising a fat component havingless than 0.5 g per serving of trans fat, and having a cyclodextrin,wherein at least about 25% of the cyclodextrin in the composition isbound to the fat. Methods of using these food products comprisingheating these food products by the non-manufacturing consumer areadditionally provided. In such methods, the consumer can realize thebenefit of having a convenient product having a fat composition with thedesired viscosity and cooking behavior, while simultaneously having lowlevels of trans fat. In additional embodiments, the food product issubstantially free of free cyclodextrin and/or is substantially free ofsaturated fat.

In another aspect of the present invention, a method of preparing athickened fat composition is provided. In this method, a cyclodextrin issolubilized in solvent, and then a fat component is mixed with thesolvent-solubilized cyclodextrin to form a fat/cyclodextrin/solventmixture. This fat/cyclodextrin/solvent mixture is separated intoseparate portions, wherein at least one portion is a thickenedfat/cyclodextrin composition comprising fat that has been complexed withcyclodextrin. In this thickened fat/cyclodextrin composition, at leastabout 25% of the cyclodextrin is bound to the fat. The thickenedfat/cyclodextrin composition is then segregated from the remainingportions of the fat/cyclodextrin/solvent mixture.

In an alternative method of preparing a thickened fat composition, acyclodextrin is solubilized in a solvent. The solubilized cyclodextrinis added to a fat at an addition rate that is sufficiently slow and withsufficient agitation to provide a thickened fat/cyclodextrin compositioncomprising fat that has been complexed with cyclodextrin. At least about25% of the cyclodextrin in the thickened fat/cyclodextrin composition isbound to the fat.

In another aspect of the present invention, it has surprisingly beenfound that very efficient binding of cyclodextrin to fat can be achievedby carrying out the complexation steps in a selected manner. Theresulting fat/cyclodextrin complex provides a low trans fat content fathaving a high viscosity. In an aspect of the present invention, theresulting thickened fat has a low amount of free cyclodextrin.

In one aspect of the present invention, a method of preparing athickened fat composition is provided comprising first solubilizing acyclodextrin in a solvent and also providing a first fat composition.The first fat composition is mixed with the solubilized cyclodextrin toform a first fat/cyclodextrin/solvent mixture comprising a firstfat/cyclodextrin complex. The temperature difference between the firstfat composition and the solubilized cyclodextrin at the initial time ofmixing is less than or equal to about 15° C. This methodology producesboth superior manufacturing efficiency and additionally can provide moreconsistent and better performing thickened and/or hardened fat products.The above described methods wherein the fat/cyclodextrin/solvent mixtureis separated into separate portions or the solubilized cyclodextrin isadded to a fat at an addition rate that is sufficiently slow and withsufficient agitation to provide a thickened fat/cyclodextrin compositioncomprising fat that has been complexed with cyclodextrin also benefitfrom carrying out the initial mixing of the fat composition and thesolubilized cyclodextrin at a temperature difference is less than orequal to about 15° C.

BRIEF DESCRIPTION OF THE DRAWINGS

FIG. 1 is a graph showing hardness data measured by a TA.XT Plus TextureAnalyzer for a blend of canola oil and palm oil thickened withalpha-cyclodextrin relative to the same proportional blend of theconstituent oils.

DETAILED DESCRIPTION

A particular benefit of the present invention is that the fat providedherein does not rely on hydrogenation of fat to provide a thickened fat.In an aspect of the present invention, the fat as thickened as describedherein has an Iodine Value that does not decrease more than 5% relativeto the unthickened component fats. Iodine Value may be determined by anyappropriate technique, provided that the Iodine Value of both thethickened fat and unthickened component fats are determined by the samemethod so that the percent decrease can be appropriately determined. Anexemplary methodology for measuring Iodine Value is AOCS Cd 1b-87.

In one embodiment of the present invention, the cyclodextrin is presentin an amount of from about 0.001% to about 75% by weight of the fatcomponent. In another embodiment, the cyclodextrin is present in anamount of from about 0.05% to about 15% or 1% to about 10% by weight ofthe fat component. In another embodiment, the fat component is selectedsuch that it has a viscosity less than about 12,500 cP at roomtemperature (i.e. 25° C.) measured relative to part number 12500 cpsavailable from Brookfield Engineering Laboratories, Inc., 11 CommerceBoulevard, Middleboro, Mass., USA, 02346, and the cyclodextrin ispresent and bound to the fat in an amount sufficient to exhibit aviscosity of a composition consisting of the fat component and thecyclodextrin that is greater than 2 times the viscosity of the fatcomponent without the cyclodextrin. In additional such embodiments, theviscosity of a composition consisting of the fat component and thecyclodextrin is greater than 10 times, 20 times or 30 times theviscosity of the fat component without the cyclodextrin. In anotherembodiment of the invention, the viscosity of the fat/cyclodextrincomposition is greater than about 12,500 cP at room temperature (i.e.25° C.) measured relative to part number 12500 cps available fromBrookfield Engineering Laboratories, Inc., 11 Commerce Boulevard,Middleboro, Mass., USA, 02346, and the cyclodextrin is present and boundto the fat in an amount sufficient to exhibit a hardness of acomposition consisting of the fat component and the cyclodextrin that isgreater than 2 times the hardness of the fat component without thecyclodextrin. In additional such embodiments, the hardness of acomposition consisting of the fat component and the cyclodextrin isgreater than 10 times, 20 times or 30 times the hardness of the fatcomponent without the cyclodextrin.

Compositions are also provided wherein the cyclodextrin is present andbound to the fat in an amount sufficient to provide a composition thathas a Solid Fat Content at 21.1° C. that is at least about 1% higherthan the Solid Fat Content at 21.1° C. of the fat component without thecyclodextrin. In additional such embodiments, the composition has aSolid Fat Content at 21.1° C. that is at least about 5%, about 8% higheror alternatively at least about 10% higher than the Solid Fat Content at21.1° C. of the fat component without the cyclodextrin.

In an embodiment of the invention, at least about 50% of thecyclodextrin in the composition is bound to the fat. In additionalembodiments of the invention, least about 75% or 90% of the cyclodextrinin the composition is bound to the fat.

The cyclodextrin in one embodiment of the present invention comprisesalpha-cyclodextrin, beta-cyclodextrin, gamma-cyclodextrin, or mixturesthereof. Cyclodextrins comprise a doughnut shaped or cyclical structurecomposed of a number of alpha-D-glucose units (typically 6-8) having ahydrophilic exterior and a hydrophobic interior. Cyclodextrins aregenerally water soluble, although alpha-cyclodextrin is likely morewater soluble than beta-cyclodextrin or gamma-cyclodextrin, and freeflowing crystalline powders that are substantially if not completelyodorless and white in color.

In one embodiment of the invention, at least a portion and preferablysubstantially all the cyclodextrin is alpha-cyclodextrin.Alpha-cyclodextrin is a cyclized ring of six alpha 1,4 linked glucoseunits. Alpha-cyclodextrin has a cavity dimension of about 0.50×0.79(nm). The solubility of alpha-cyclodextrin in water is good and at 25°C. is about 14 (gm/100 mL). In contrast, the native solubility ofcyclodextrins in fats is poor. A useful alpha-cyclodextrin iscommercially available in the United States from Wacker Specialties,Adrian, Mich. 49221 and sold under the trademark CAVAMAX® W6Wacker-Chemie, Burghausen, Germany.

In another embodiment of the invention, alpha-cyclodextrin is used incombination or synergistically with beta-cyclodextrin and/orgamma-cyclodextrin, in particular ratios dependent upon the requirementsof the ultimate user. In an exemplary embodiment, alpha-cyclodextrin canbe used individually or can be combined with between 0-50% by weightbeta-cyclodextrin or gamma-cyclodextrin or with between 0.1 to about 40%by weight beta-cyclodextrin. Beta-cyclodextrins and gamma-cyclodextrinsare also available from Wacker Specialties, Adrian, Mich., USA, 49221.

One method of preparing cyclodextrins includes enzymatic treatment.Enzymatic degradation or treatment of the starch to producecyclodextrins useful in the present invention is done through the use ofcyclodextrin glucosyltransferase (CGTase, EC 2.4.1.19) or other enzymes,which results in a cyclic ring of sugar. In one method, cyclodextrinsare produced by the action of cyclodextrin glucosyltransferase onhydrolyzed starch syrups at neutral pH (6.0-7.0) and moderatetemperature (35-40° C.). Alternatively, cyclodextrins can be produced inplanta by the expression of the gene encoding CGTase in the food plantof interest.

In preparation of the cyclodextrin/fat composition, fat components canbe selected from oils and shortenings. Examples of such oils can includeoil ingredients from vegetable, dairy and marine sources includingbutter oil or butterfat, soybean oil, corn oil, rapeseed or canola oil,copra oil, cottonseed oil, fish oil, safflower oil, olive oil, sunfloweroil, peanut oil, palm oil, palm kernel oil, coconut oil, rice bran oiland other plant derived oils such as vegetable or nut oils. Examples ofshortenings include animal fats such as lards, butter and hydrogenatedvegetable oils such as margarine. Mixtures of different fats are alsocontemplated.

In an embodiment of the invention, the fat comprises an oil selectedfrom soybean oil, high-oleic sunflower oil, high-linoleic soybean oil,palm oil, palm kernel oil or coconut oil. Particularly advantageous oilsinclude low linolenic, high stearic soybean oil; canola oil; high or midoleic canola oil; high or mid oleic sunflower oil, rice bran oil; andhydrogenated rapeseed oil.

An alternative fat composition comprises fat having a viscosity greaterthan about 12,500 cP at room temperature (i.e. 25° C.) measured relativeto part number 12500 cps available from Brookfield EngineeringLaboratories, Inc., 11 Commerce Boulevard, Middleboro, Mass., USA,02346. An embodiment of a fat has a Solid Fat Content of greater than 15at 21.1° C. Examples of solid fat compositions include animal fats suchas lard, butter, and hydrogenated vegetable oils such as margarine.

The fats can be emulsified or stabilized with mono- or diglycerides orother emulsifiers known in the art. Examples of emulsifiers includefully hydrogenated soybean oil mono-, di-, or tri-glyceride; mono-, di-,or tri-stearate, sodium stearyl-2-lactylate, and mixtures thereof.

Additionally, the fat/cyclodextrin composition can comprise adjuvantssuch as colorants, flavorants, texture modifiers, preservatives,stabilizers, and the like, designed to improve the taste, appearance andnutritional properties of the finished products. If present, each suchadjuvant ingredient can in one embodiment of the invention be present inan amount ranging from about 0.01% to about 5% of the thickened fatproduct

The present thickened fat ingredients find particular suitability foruse in connection with consumer food products. While particularattention is thus paid to such consumer food products in the presentdescription, the skilled artisan will appreciate that the invention alsocan find suitability for use in connection with other productapplications. For example, the present application can find usefulnessin the provision of animal feed products especially for common companionanimals such as dogs and domestic cats. The thickened fat ingredientscan also find usefulness in the provision of, other non-food products,e.g., cosmetics (e.g., hand crèmes and lotions), soaps or shampoos orother viscous surfactant compositions that are based upon fattytriglycerides, e.g. paints using linseed oil as drying oil. In stillother applications, the oils can be inedible such as those that arepetroleum based.

In an embodiment of the invention, the fat-containing composition isutilized in a food product. In an embodiment of the invention, the foodproduct is provided as a packaged food product, either in bulk, inmultiple servings (i.e. from about 2 to about 20 servings) or as singleserving. The thus packaged food product can be provided in the cookedstate, or the uncooked state. Examples of such food products includethose that are packaged for heating by a non-manufacturing consumer. Thephysical and organoleptic properties of the fat-containing compositionas described herein can provide particular benefit in such food productsdue to their shelf stability, excellent performance under a variety ofenvironmental conditions. One particular example of a food productfinding benefit of the present invention is related to products that arepackaged for microwave heating.

Thus, the present invention provides a method of using the food productwherein the food product is packaged for subsequent heating of the foodproduct by a non-manufacturing consumer. For purposes of the presentinvention, a “non-manufacturing consumer” is a party that does notassemble the raw ingredients of the food product, but instead canundertake one or more subsequent food preparation operations such assubdividing the food product into smaller portions and heating andoptionally applying auxiliary ingredients such as sauces and the like tothe food product. Examples of such non-manufacturing consumers includeinstitutional food providers such as school cafeterias and hospitals andthe like, and restaurants and the like. A sub-group of thenon-manufacturing consumer is the retail customer, who is the individualparty purchasing the food product for non-commercial use, such asfeeding the family in the home. In an embodiment of the invention, thefood product is provided as a packaged food product, either in bulk, inmultiple servings (i.e. from about 2 to about 20 servings) or as singleserving.

In one embodiment, this packaging is for microwave heating of the foodproduct by a non-manufacturing consumer. In a specific example of thisembodiment, the food product is packaged in a package suitable forplacement in a microwave oven. In a more specific example, the packageis designed to assist in cooking of the food product in a microwaveoven.

An example of a food product includes laminated dough products. Otherexamples of food products included biscuits, croissants, crescent rolls,cookies, cereals and cereal based products (particularly ready to eat(“R-T-E”) cereals i.e. grain or vegetable based products in the form offlakes, extruded shapes or puffed, and optionally containing fruitsand/or nuts or other such ingredients, such as corn flakes, puffedwheat, puffed rice, raisin bran flakes, and the like), cakes, snackbars, cereal bars, granola bars, bread products (such as loaf breads,rolls, and buns), and the like. Another example of a food product is atablespread, such as butter or margarine, and in particular flavoredspreads.

The thickened fat can be used as an ingredient or phase of a foodproduct. For example, a fondant composition comprising the thickened fatand sugars (e.g., powdered sugar) can be used as a topical ingredient ora food phase (e.g., as a crème center to baked cookie wafers or othercookies or to a granola bar) or as a coating or icing for a variety offinished baked goods. The fondant can be the center of a filled candy orchocolate such as truffles. If desired, the fondant can also be aerated.In other food use applications, the thickened fat can be employed as aningredient in a fat and oil, e.g., a peanut butter whose oil ingredientdoes not separate even though non-hydrogenated.

In other variations, the thickened fat can be saponified with an alkalisuch as sodium or potassium hydroxide to make a thickened vegetable oilsoap.

In still other variations, the thickened fats can be used as aningredients in various emulsions whether water-in-oil (“w/o”) oroil-in-water (“o/w”) in both food and non-food applications.

In a method of the present invention, a cyclodextrin is firstsolubilized in solvent. Generally, the cyclodextrin is added to solventin an amount up to the solubility of the cyclodextrin in the solvent atthe temperature of mixing. The solvent used for solvation of thecyclodextrin can be any solvent suitable for processing of theparticular product to be prepared. For example the solvent desirably issafely consumable without adverse health concerns, or is readily removedfrom the product prior to consumption. Examples of particularly suitablesolvents include water, alcohol, and mixtures of water and alcohol.Examples of alcohols particularly desired for use in the presentinvention include an edible alcohol such as non denatured ethanol ormixtures of water and ethanol. In additional embodiments, the water isat least deionized water and is preferably distilled water. Thus, atroom temperature a typical process will include adding and mixingcyclodextrin to water in an amount of about 14% cyclodextrin by weight.In an embodiment that provides excellent performance results, thecyclodextrin is solubilized in solvent at a cyclodextrin:solvent mixratio of from about 0.01:1 to about 5:1 by weight, respectively. Fat isthen mixed with the cyclodextrin-water mixture preferably in liquid form(e.g., added at a temperature above its melting point) and preferablywith vigorous agitation for durations sufficient to form a slurry ofcyclodextrin at least partially complexed with the fat ingredient.

This mixture is caused to separate into separate portions especiallyinvolving mechanical separation, wherein one portion is a thickenedfat/cyclodextrin composition comprising fat that has been complexed withcyclodextrin. The separation step can include any appropriate technique,such as churning, centrifuging, hydrocyclone processing, decanting, andthe like. At least about 25% of the cyclodextrin in this thickenedfat/cyclodextrin composition is bound to the fat. The thickenedfat/cyclodextrin composition is segregated from the remaining portionsof the fat/cyclodextrin/solvent mixture. The preparation method can bepracticed at any suitable temperature, including temperatures rangingfrom about 5° C. to about 100° C. at atmospheric pressure. As notedabove, in an embodiment of the invention, the solubilized cyclodextrinis mixed with the fat composition when the fat is in the form of aliquid above its melting point to facilitate the formation of thecyclodextrin fat complex.

In an embodiment of the invention, the fat/cyclodextrin/solvent mixtureis separated by centrifuging the mixture for a time and at a speedsufficient to separate the mixture into portions that are segregatablelayers. This centrifuging operation can be carried out at anyappropriate temperature. In one embodiment, the centrifuging operationis carried out at a temperature of about 5 to 25° C.

The segregatable layers can be characterized in any way appropriate toidentify the desired portion for the particular use of the ultimate fatcomposition. For example, the fat/cyclodextrin/solvent mixture can beseparated into at least first, second and third portions based upondensity. In this embodiment, the first portion or lightest or leastdense portion can be a thickened fat/cyclodextrin composition comprisingfat that has been complexed with cyclodextrin, wherein at least about25% of the cyclodextrin in the thickened fat/cyclodextrin composition isbound to the fat, the first portion having a density less than 1 g/ml.The second portion can be a more dense aqueous phase containingsolubilized cyclodextrin. The third portion or heaviest portion can be athickened fat/cyclodextrin composition comprising fat that has beencomplexed with cyclodextrin, the third portion having a density greaterthan 1 g/ml. In this embodiment, the first and third portions can findparticular utility in various food products, where the removal of thesecond portion in this process assures that a low level of unboundcyclodextrin is present in the ultimate food product. Previouscompositions comprising both cyclodextrin and fat did not contemplateremoval of uncomplexed cyclodextrin as provided herein.

The desired layer for use in various products can be segregated from theother layers in any appropriate manner, such as decanting, pumping ordraining. For example in the three layer embodiment as discussed above,material can be removed from the top layer to segregate the firstportion. Alternatively, material can be removed from the middle layer toremove the second portion, with optional subsequent mixing of the topand bottom layer to provide a composition that is a mixture of the firstand third portions. Alternatively, material can be removed from thebottom layer to segregate the third portion. Optionally, the secondportion, which comprises unbound cyclodextrin, can be reused insubsequent processes to provide high efficiency use of available rawmaterials.

In an embodiment of the invention, the method additionally comprises thestep of removing solvent from the thickened fat/cyclodextrin compositionto an amount of less than about 20%, 10% or 5% by weight of the totalthickened fat/cyclodextrin composition. In other embodiments,substantially all moisture is removed from the thickened fat (i.e., toprovide a moisture content of less than 1%). Removal of solvent can becarried out by any appropriate drying technique process, such as spraydrying, paddle drying, drum drying, freeze drying, or evaporation ofsolvent by bulk heating.

In another embodiment of the invention, cyclodextrin is solubilized in asolvent, and the solubilized cyclodextrin is added to a fat at anaddition rate that is sufficiently slow and with sufficient agitation toprovide a thickened fat/cyclodextrin composition comprising fat that hasbeen complexed with cyclodextrin. At least about 25% of the cyclodextrinin the thickened fat/cyclodextrin composition is bound to the fat.

As above, the solvent used for solvation of the cyclodextrin can be anysolvent suitable for processing of the particular product to beprepared. For example the solvent desirably is safely consumable withoutadverse health concerns, or is readily removed from the product prior toconsumption. Examples of particularly suitable solvents include water,alcohol, and mixtures of water and alcohol. The cyclodextrin can beprovided in any desired weight ratio relative to the solvent. Examplesof desired weight ratios include from about 1:10 to about 10:1, or fromabout 5:1 to about 1:5, or from about 2:1 to about 1:2 of cyclodextrinto solvent.

In an embodiment of the invention, the addition of the solubilizedcyclodextrin to the fat can be carried out at a temperature of fromabout 4° C. to about 95° C., and in another embodiment from about 30° C.to about 80° C. It is contemplated that the addition of the solubilizedcyclodextrin to the fat can be carried out under an inert atmosphere,such as nitrogen. Either the solubilized cyclodextrin and/or the fatadditionally optionally can comprise an emulsifier, such as palmdistilled monoglycerides.

In embodiments of the present invention, the resulting thickenedfat/cyclodextrin composition can comprise up to about 40%, of solvent(and particularly water) by weight. In other embodiments, the resultingthickened fat/cyclodextrin composition can comprise less than about 20%,or 10%, or 5% of solvent (and particularly water) by weight.Advantageously, this method facilitates achievement of a low solventcontent as a function of the total thickened fat/cyclodextrincomposition by optionally limiting the amount of solvent that is addedto the fat in the first place. Alternatively, excess solvent may beadded, and subsequently removed by solvent removal processes asdiscussed above. This method of manufacture thus can provide substantialbenefit in reduction of costs that would otherwise be incurred in thesolvent removal process, and in providing a simple manufacturing processthat does not necessitate investment in capital equipment such ascentrifuges and the like for manufacture of the desired thickenedfat/cyclodextrin composition.

As noted above, it has surprisingly been found that superiormanufacturing efficiency that can result in better performing thickenedand/or hardened fat products are provided by the manufacturingmethodology described herein. More specifically, a method of preparing athickened fat composition is provided comprising first solubilizing acyclodextrin in a solvent and also providing a first fat composition.

The first fat composition is mixed with the solubilized cyclodextrin toform a first fat/cyclodextrin/solvent mixture comprising a firstfat/cyclodextrin complex. The temperature difference between the firstfat composition and the solubilized cyclodextrin at the time of mixingis less than or equal to about 15° C.

In one embodiment, the temperature of the first fat composition isgreater than or equal to the temperature of the solubilized cyclodextrinat the time of mixing.

The method can in one embodiment be carried out wherein the first fatcomposition is a fat from only one source and contains substantially noadditional fats. In another embodiment, the first fat compositioncomprises only a single fat, and substantially no additionalingredients. Alternatively, the method can be carried out wherein thefirst fat composition comprises a mixture of fats.

In one embodiment, the present method contemplates mixing a second fatcomposition with the first fat/cyclodextrin/solvent mixture afterformation of the first fat/cyclodextrin complex. In this embodiment, thesecond fat composition is not complexed with cyclodextrin. In anotherembodiment, the present method contemplates carrying out a separate fatcomplexation process with a second fat composition. In other words,providing a second fat composition and mixing the second fat compositionwith the solubilized cyclodextrin to form a secondfat/cyclodextrin/solvent mixture comprising a second fat/cyclodextrincomplex, wherein the temperature difference between the second fatcomposition and the solubilized cyclodextrin at the time of mixing isless than or equal to about 15° C. Subsequently, the firstfat/cyclodextrin complex is mixed with the second fat/cyclodextrincomplex. This embodiment finds particular benefit where it is desirableto complex both fats in a fax mixture, but the rate of complexation ofthe two fats with cyclodextrin is sufficiently different that one fatwould be complexed more than the other if it was attempted to complexboth in the same reaction vessel.

It has additionally been discovered that the temperature at whichoptimal complexation takes place of any given fat with cyclodextrin inthe present method may be uniquely identified for each fat. Thus, it hassurprisingly been found that palm oil generally favorably complexes withcyclodextrin in the present method at about 50° C. In one embodiment,the first fat composition comprises palm oil, and the temperature ofeach of the first fat composition and the solubilized cyclodextrin atthe time of mixing is from about 35° C. to about 65° C. Similarly, ithas surprisingly been found that canola oil generally favorablycomplexes with cyclodextrin in the present method at about 15° C. In oneembodiment, the first fat composition comprises canola oil, and thetemperature of each of the first fat composition and the solubilizedcyclodextrin at the time of mixing is from about 0° C. to about 30° C.In one aspect of the present invention, the temperature at which optimalcomplexation takes place of any given fat composition with cyclodextrinin the present method is determined through experimentation that withknowledge of the present disclosure will now be recognized to beroutine, and carrying out the complexation method of the presentinvention within about 15° C. of that optimal complexation temperature.

It has additionally been determined that it is advantageous to carry outthe mixing step of the fat composition and the solubilized cyclodextrinand then to hold the composition for a period of at least about 30minutes. Thus, for example, the first fat composition can comprise palmoil, and the temperature of each of the first fat composition and thesolubilized cyclodextrin at the time of mixing is from about 35° C. toabout 95° C., and after mixing, the fat/cyclodextrin/solvent mixture isheld at a temperature of from about 35° C. to about 95° C. for a periodof at least about 30 minutes. In another example, the first fatcomposition comprises canola oil, and the temperature of each of thefirst fat composition and the solubilized cyclodextrin at the time ofmixing is from about 4° C. to about 80° C., and after mixing, thefat/cyclodextrin/solvent mixture is held at a temperature of from about0° C. to about 80° C. for a period of at least about 30 minutes.

Additionally, it surprisingly has been determined that it isadvantageous to carry out the mixing step of the fat composition and thesolubilized cyclodextrin at an initial mixing temperature that is atleast about 15° C. higher than the optimal complexation temperature ofthe fat composition, and then allowing the composition to cool and beheld within about 15° C. of the optimal complexation temperature of thefat composition for a period of at least about 30 minutes. Thus, in oneembodiment, the first fat composition comprises palm oil, and thetemperature of each of the first fat composition and the solubilizedcyclodextrin at the time of mixing is from about 50° C. to about 90° C.,(and in another embodiment, from about 70° C. to about 90° C.), andafter mixing, the fat/cyclodextrin/solvent mixture is held at atemperature of from about 35° C. to about 65° C. for a period of atleast about 30 minutes. Similarly in another embodiment, the first fatcomposition comprises canola oil, and the temperature of each of thefirst fat composition and the solubilized cyclodextrin at the time ofmixing is from about 60° C. to about 80° C., and after mixing, thefat/cyclodextrin/solvent mixture is held at a temperature of from about0° C. to about 30° C. for a period of at least about 30 minutes.

In an embodiment of the present invention, the ratio of cyclodextrin tofirst fat composition is about 1-5% by weight. In another embodiment,the solubilized cyclodextrin is added to the first fat composition insequential additions. The amount of the solubilized cyclodextrin to beadded to the fat composition can be precalculated. In an alternativeembodiment, it is noted that variations in material behavior andappropriate mix ratios may come about due to different material sourceor handling factors, and that a preset calculation may not be asaccurate or uniform as desired. An advantageous alternative embodimentof the present invention therefore is to determine the amount of thesolubilized cyclodextrin to be added to the fat composition byin-process measurement of viscosity of the fat/cyclodextrin/solventmixture until a predetermined target viscosity is reached.

In all embodiments, an advantageous embodiment of the present methodprovides that the solubilized cyclodextrin is added to the first fatcomposition under shear mixing conditions.

Food products can advantageously be formulated using fat compositions asdescribed herein, wherein cyclodextrin is bound to the fat. Reducedamount of unbound cyclodextrin in intimate contact with fat isparticularly advantageous, as noted above, in reduction of thegeneration of undesirable cyclodextrin residues. It is specificallycontemplated that food products can additionally comprise cyclodextrinthat is not bound to fat, and additionally is not in intimate contactwith fat as a separate additive to the food product. For example,cyclodextrin that is not bound to fat and not in intimate contact withfat can be added as a component of encapsulated flavorants, forsequestering of bile acids as taught in U.S. patent application Ser. No.10/172,471, filed Jun. 14, 2002, titled “FOOD PRODUCT HAVING INCREASEDBILE ACID BINDING CAPACITY,” LEWANDOWSKI ET AL; for reduction ofgeneration of acrylamides in food products as taught in U.S. patentapplication Ser. No. 10/630,489, filed Jun. 22, 2003, titled “TREATMENTCOMPOSITION FOR REDUCING ACRYLAMIDE IN FOOD PRODUCTS AND FOODINTERMEDIATES,” PLANK ET AL; or for reduction of cholesterol as taughtin U.S. patent application Ser. No. 10/318,445 Filed Dec. 13, 2002,titled “FOOD PRODUCTS CONTAINING CYCLODEXTRINS HAVING BENEFICIALHYPOCHOLESTEROLEMIC EFFECTS AND METHOD OF MAKING AND COMMUNICATING THEBENEFIT OF SUCH PRODUCTS,” PLANK ET AL.

In an embodiment of the present invention, the food product as describedherein is provided and additionally, at least one indicium is preparedconcerning the beneficial effect of the food product. The indicia arereleased to consumers, thereby informing the consumer of the surprisinglow trans-fat and optionally low saturated fat content of the foodproduct. The indicia can optionally be provided in audio or visualmedia. The release of such indicia is usually tailored to certainpre-selected or predefined formats and can be done through traditionaladvertising routes that have at least an audio capability such as radioand television as well printed materials. Printed materials can includethe packaging into which the product is placed as well as newspapers,letters, direct mail pieces, magazines and the like. This informationempowers individuals to make choices regarding the food that theyconsume, thereby enabling an alteration of the behavior of individuals.Thus, the knowledge of the benefit of the food product of the presentinvention does not merely inform consumers that the food is good forthem, but rather facilitates choice in the total diet to either selectfood products that will reduce trans-fat and/or saturated fatconsumption by the consumer or to permit consumption of additional foodshaving higher trans-fat and/or saturated fat content than wouldotherwise be permitted to the consumer who is carefully monitoringtrans-fat and/or saturated fat intake.

The invention will further be described by reference to the followingnonlimiting examples.

EXAMPLES Test Protocols

A. Hardness and Spreadability

Hardness can be measured by the force required to obtain a givendeformation or by the amount of deformation under a given force.Spreadability is the ease with which a fat can be applied in a thin,even layer to a substrate, such as bread. Although spreadability is alsoa deformation under an external load, it is a more dynamic property.Measurements of hardness and spreadability are usually highlycorrelated. Some differences can be observed, however, as a function ofthe impact of worksoftening on the physical characteristics of theparticular fat.

The parameters of hardness and spreadability can be applied todistinguish hardened fats like those produced from complexation withcyclodextrins. A fat or oil thickened with a cyclodextrin will showincreases in either hardness, spreadability or both relative to the samefat or oil without added cyclodextrin.

A Model TA.XT Plus Texture Analyzer from Stable Micro Systems, Ltd. isused to measure both hardness and spreadability. The TTC SpreadabilityFixture is a set of precisely matched male and female Perspex™ 90°cones. The material is allowed to set up in the lower cone or is filledinto the lower cone with a spatula. The material is pressed down only somuch as is needed to eliminate air pockets which are visible through thePerspex™ cones, and then the surface is leveled with a flat knife.Excessive work is not introduced into the product. The samples areallowed to equilibrate to the specified temperature (e.g. 23° C.) beforetesting.

As seen in FIG. 1, the peak force in the positive direction (hardness)and the total area under the positive curve (spreadability) is greaterfor a 50:50 blend of canola oil and palm oil thickened with about 2.5%by weight of alpha-cyclodextrin relative to the same proportional blendof the constituent oils. In this instance, the magnitude of the negativepeak and area are also increased for the blend of canola oil and palmoil thickened with alpha-cyclodextrin relative to the proportional blendof constituent oils, indicating an increase in adhesion or stickinesswhen alpha-cyclodextrin is incorporated therein.

B. Determination of Alpha-Cyclodextrin in Fat-Containing Food Products

-   Solution A: 0.1 M acetic acid    -   0.7% (w/w) KCl    -   99.3% ddH₂0-   Solution B: 2:1 Chloroform:Methanol-   Reagent 1: Glyceryl triheptadecanoate (Sigma Prod # T2151-1G)-   HPLC System: Column: Superdex Peptide 10/300 GL (Amersham    Biosciences)    -   Flow Rate: 0.5 ml/min    -   Buffer A: 100 mM KH₂PO₄, pH 6.9 filtered and degassed.    -   Monitors: UV/V is diode array 215 nm (Beckman-Coulter, Model        168, Fullerton, Calif. 92835)        -   Refractive Index detector (HP Model 1047A, Agilent            Technologies Palo Alto, Calif. 94303 USA)    -   Pump: Beckman-Coulter Model 126, (Beckman-Coulter, Fullerton,        Calif. 92835))    -   Autosampler: Beckman-Coulter Model 508 (Beckman-Coulter,        Fullerton, Calif. 92835)    -   Data analysis: Beckman 32 karat, (Beckman-Coulter, Fullerton,        Calif. 92835)-   Gas Chromatography System:    -   Gas Chromatograph: Agilent Model HP 6890 GC System    -   Column: Agilent Model 122-2362, J&W Scientific DB-23        -   Durobond FS02 Capillary Column 60 m×0.25 mm.        -   Film thickness: 0.25 um        -   Mode: Constant Flow; Initial Flow: 2.1 mL/min        -   Nominal initial pressure: 32.71 psi        -   Average velocity: 33 cm/sec    -   Inlet:        -   Mode: Split        -   Initial temperature: 250 C        -   Pressure: 32.70 psi        -   Split ratio: 50:1        -   Split flow: 104.9 mL/min        -   Total flow: 108.6 mL/min        -   Gas Type: Helium    -   Flame Ionization Detector:        -   Temperature: 260 C        -   Hydrogen flow: 40.0 mL/min        -   Air flow: 450 mL/min        -   Mode: Constant makeup flow        -   Makeup flow: 45.0 mL/min        -   Makeup gas type: Helium    -   Oven:        -   Initial Temp: 50 C Max Temp: 280 C        -   Initial Time: 1.00 min Equilibration time: 0 min        -   Ramps:

# Rate Final Temp Final Time 1 25.00 175 0.00 2  4.00 230 5.00 3 10.00250 10.00 4 0.0 (off)

-   -   -   Post temp: 100 C        -   Post time: 0.00 min        -   Run time: 36.75 min

    -   Data analysis:        -   GC Chemstation A.10.01, Agilent Technologies, Inc., 5301            Stevens Creek Boulevard, Santa Clara, Calif., USA 95051            Method 1A (Macro Method for Foods and Fats with            Non-Ionizable Triglycerides)

-   1. Weigh out 1.000 gram of food sample to each of two clean 250 ml    glass screw cap Erlenmeyer flasks with phenolic foil lined caps    (“Flask”) and record weight.

-   2. Add Reagent 1, Glyceryl triheptadecanoate, (1.0 mg) to the Flask.

Determination of Unbound Alpha-Cyclodextrin

-   3. Add 20.0 ml of ddH₂O.-   4. Heat Sample at 40° C. for 30 minutes.-   5. Cool sample to room temperature.-   6. Centrifuge one aqueous sample at 5000×g. Use the other aqueous    sample as described in 10 below.-   7. Filter 1 ml of the centrifuged sample supernatant with 0.45    micrometer nylon filter. Inject on to HPLC molecular sizing column.-   8. Take 10 ml of sample from 6 above and concentrate by    roto-evaporator to 1 ml (record exact volumes). Filter with 0.45    micrometer nylon filter. Inject on to HPLC molecular sizing column.-   9. For Pure Fat Samples Only: Weigh remainder of supernatant sample    into tared flask. Evaporate moisture to dryness. Record weight of    solids. (note: net weight for non-salt containing fat samples will    represent free alpha-cyclodextrin)

Extraction of Fat and Determination of Total Alpha-Cyclodextrin

-   10. Add 10 ml of 2:1 Chloroform:MeOH to 2^(nd) flask 20 ml Vial.    Seal cap tightly. Incubate at 40° C. for 1 hour with constant    shaking at 250 rpm.-   11. Focus organic and aqueous phase by centrifuging for 10 min at    5000 rpm separating the organic phase from the aqueous phase.-   12. Withdraw bottom layer (chloroform:MeOH) from the flask avoiding    the aqueous layer during the draw. Transfer to a clean flask and dry    down and treat as in 13 below.

Determination of Total Fat by Gas Chromatography

-   13. Resolubilize dried organic phase sample from 12 above with    appropriate amount of chloroform (0.5 to 0.9 ml). Transesterify    using Alltech MethPrep II (Alltech Associates, Inc., Deerfield, Ill.    60015, USA) or sodium methoxide. Alternatively, saponify samples.-   14. Silanate samples (optional for glycerol and sterol    determination) and inject on to GC with FID detector or Mass Spec    detector (Hewlett Packard Model 5970 MSD; Agilent Technologies Palo    Alto, Calif. 94303 USA) to quantify or determine the amount fat or    level of sterol related compounds that are found in sample.

Determination of Total (Bound+Unbound) Alpha-Cyclodextrin

-   15. Centrifuge the isolated aqueous layer from 12 above at 5000×g.-   16. Filter 1 ml of the centrifuged sample supernatant with 0.45    micrometer nylon filter. Inject on to HPLC molecular sizing column.    Quantify total cyclodextrin relative to a response factor developed    from a standard curve of pure cylcodextrin.-   17. For Pure Fat Samples Only: Weigh remainder of supernatant sample    into tared flask. Evaporate moisture to dryness. Record weight of    solids. (note: net weight for non-salt containing fat samples will    represent free alpha-cyclodextrin)-   18. Subtract free alpha-cyclodextrin amounts determined in 7 and 8    above from values determined in steps 18 and 19, respectively. Value    equals total bound alpha-cyclodextrin.    Method 2A (Micro Method for Foods and Fats with Non-Ionizable    Triglycerides)-   1. Weigh out 0.1000 gram of sample each into two clean 20 ml glass    scintillation vial with phenolic foil lined cap (“Vial”) and record    weight.-   2. Add Reagent 1, Glyceryl triheptadecanoate, (0.1 mg) Weigh out    0.1000 gram of sample into each Vial.

Extraction of Unbound Alpha-Cyclodextrin

-   3. Add 2.0 ml of ddH₂O.-   4. Heat Samples at 40° C. for 30 minutes.-   5. Cool sample to room temperature.-   6. Centrifuge one aqueous sample at 5000×g. Use the other aqueous    sample as described in 8 below.-   7. Filter 1 ml of the centrifuged sample supernatant with 0.45    micrometer nylon filter. Inject on to HPLC molecular sizing column.    Determine quantity of alpha-cyclodextrin by integrating peak at    approximately 32 minute retention time. Quantify total cyclodextrin    relative to a response factor developed from a standard curve of    pure cylcodextrin. (Note: The retention time will vary depending on    volume of HPLC system. The retention time for a given system should    be determined by calibration using a standard of pure cyclodextrin)

Extraction of Fat and Bound Alpha-Cyclodextrin

-   8. Add 10.0 ml of 2:1 Chloroform:MeOH. Seal cap tightly. Incubate at    40° C. for 1 hour with constant shaking at 250 rpm.-   9. Focus organic and aqueous phase by centrifuging for 10 min at    5000 rpm separating the organic phase from the aqueous phase.-   10. Withdraw bottom layer (chloroform:MeOH) from the vial with a 10    ml gas tight syringe. Avoiding the aqueous layer during the draw.    Transfer to a clean flask and dry down.-   11. Resolubilize sample from 10 above with appropriate amount of    chloroform (0.5 to 0.9 ml). Transesterify using Alltech MethPrep II    (Alltech Associates, Inc., Deerfield, Ill. 60015, USA) or sodium    methoxide. Alternatively, saponify samples.-   12. Silanate samples (optional for glycerol and sterol    determination) and inject on to GC with FID detector or Mass Spec    detector (Hewlett Packard Model 5970 MSD; Agilent Technologies Palo    Alto, Calif. 94303 USA) to quantify or determine the amount or level    of sterol related compounds that are found in sample.

Determination of Total (Bound+Unbound) Alpha-Cyclodextrin

-   13. Centrifuge the isolated aqueous layer from 10 above at 5000×g    for 10 min.-   14. Filter 1 ml of the centrifuged sample supernatant with 0.45    micrometer nylon filter. Inject on to HPLC molecular sizing column.    Quantify total cyclodextrin relative to a response factor developed    from a standard curve of pure cylcodextrin.-   15. For Pure Fat Samples Only: Weigh remainder of supernatant sample    into tared flask. Evaporate moisture to dryness. Record weight of    solids. (note: net weight for non-salt containing fat samples will    represent free alpha-cyclodextrin)-   16. Subtract free alpha-cyclodextrin amounts determined in 7 above    from values determined in steps 14 and 15. Value equals total bound    alpha-cyclodextrin.    Method 3A (Micro Method for Foods and Fats with Ionizable    Triglycerides, e.g. Phoshatidyl Choline, etc.)-   1. Weigh out 0.1000 gram of sample each into two clean 20 ml glass    scintillation vial with phenolic foil lined cap (“Vial”) and record    weight.-   2. Add Reagent 1, Glyceryl triheptadecanoate, (0.1 mg) into each    Vial.

Extraction of Unbound Alpha-Cyclodextrin

-   3. Add 2.0 ml of Solution A: 0.1 M Acetic Acid with 0.7% (w/v) KCl.-   4. Heat Samples at 40° C. for 30 minutes.-   5. Cool sample to room temperature.-   6. Centrifuge one aqueous sample at 5000×g. Use the other aqueous    sample as described in 9 below.-   7. Filter 1 ml of the centrifuged sample supernatant with 0.45    micrometer nylon filter. Inject on to HPLC molecular sizing column.    Determine quantity of alpha-cyclodextrin by integrating peak at    approximately 32 minute retention time. Quantify total cyclodextrin    relative to a response factor developed from a standard curve of    pure cyclodextrin. (Note: The retention time will vary depending on    volume of HPLC system. The retention time for a given system should    be determined by calibration using a standard of pure cyclodextrin)

Extraction of Fat and Bound Alpha-Cyclodextrin

-   8. Add 10.0 ml of 2:1 Chloroform:MeOH. Seal cap tightly. Incubate at    40° C. for 1 hour with constant shaking at 250 rpm.-   9. Focus organic and aqueous phase by centrifuging for 10 min at    5000 rpm separating the organic phase from the aqueous phase.-   10. Withdraw bottom layer (chloroform:MeOH) from the vial with a 10    ml gas tight syringe, avoiding the aqueous layer during the draw.    Transfer to a clean flask and dry down.-   11. Resolubilize sample from 11 above with appropriate amount of    chloroform (0.5 to 0.9 ml). Transesterify using Alltech MethPrep II    (Alltech Associates, Inc., Deerfield, Ill. 60015, USA) or sodium    methoxide. Alternatively, saponify samples.-   12. Silanate samples (optional for glycerol and sterol    determination) and inject on to GC with FID detector or Mass Spec    detector (Hewlett Packard Model 5970 MSD; Agilent Technologies Palo    Alto, Calif. 94303 USA) to quantify or determine the amount or level    of sterol related compounds that are found in sample.

Determination of Total (Bound+Unbound) Alpha-Cyclodextrin

-   13. Centrifuge the isolated aqueous layer from 11 above at 5000×g    for 10 min.-   14. Filter 1 ml of the centrifuged sample supernatant with 0.45    micrometer nylon filter. Inject on to HPLC molecular sizing column.    Quantify total cyclodextrin relative to a response factor developed    from a standard curve of pure cyclodextrin.-   15. For Pure Fat Samples Only: Weigh remainder of supernatant sample    into tared flask. Evaporate moisture to dryness. Record weight of    solids. (note: net weight for non-salt containing fat samples will    represent free alpha-cyclodextrin)-   16. Subtract free alpha-cyclodextrin amounts determined in 8 above    from values determined in steps 15 and 16. Value equals total bound    alpha-cyclodextrin.

C. Determination of Solid Fat Content of Fats and Oils

Fats containing either alpha-cyclodextrin complexed oil or the sameproportion of oil without alpha-cyclodextrin were measured for solid fatcontent using a Bruker Minispec using the American Oil Chemist's Society(AOCS) Official Method Cd 16b-93 revised 1999, Solid Fat Content (SFC)by Low-Resolution Nuclear Magnetic Resonance—The Direct Method. As canbe seen in the table below, fats containing oil complexed withalpha-cyclodextrin have consistently higher solid fat contents.

Solid Fat Content (%) Temp. Fat #1 Fat #2 Fat #3 Fat #4 Fat #5 (° C.) A¹B² A³ B⁴ A⁵ B⁶ A⁷ B⁸ A⁹ B¹⁰ 10.0 14.5 24.4 22.2 31.7 31.5 39.9 57.8 61.460.7 67.1 21.1 10.1 20.1 16.1 25.3 22.6 31.2 32.6 45.7 39.8 51.2 26.77.9 18.7 12.9 22.7 17.9 27.1 21.4 35.2 27.5 41.1 33.3 5.6 15.6 9.4 18.613.6 21.6 11.9 24.3 16.4 28.6 37.8 3.9 14.0 6.8 16.2 10.4 18.2 6.8 17.710.1 20.4 ¹Fat #1 A = 80% high oleic canola oil, 10% palm stearine, 10%mixed soybean mono and diglycerides. ²Fat #1 B = 80% alpha-cyclodextrincomplexed high oleic canola oil, 10% palm stearine, 10% mixed soybeanmono and diglycerides. ³Fat #2 A = 70% high oleic canola oil, 20% palmstearine, 10% mixed soybean mono and diglycerides. ⁴Fat #2 B = 70%alpha-cyclodextrin complexed high oleic canola oil, 20% palm stearine,10% mixed soybean mono and diglycerides. ⁵Fat #3 A = 60% high oleiccanola oil, 30% palm stearine, 10% mixed soybean mono and diglycerides.⁶Fat #3 B = 60% alpha-cyclodextrin complexed high oleic canola oil, 30%palm stearine, 10% mixed soybean mono and diglycerides. ⁷Fat #4 A = 70%palm oil, 20% palm stearine, 10% mixed soybean mono and diglycerides.⁸Fat #4 B = 70% alpha-cyclodextrin complexed palm Oil, 20% palmstearine, 10% mixed soybean mono and diglycerides. ⁹Fat #5 A = 60% palmoil, 30% palm stearine, 10% mixed soybean mono and diglycerides. ¹⁰Fat#5 B = 60% alpha-cyclodextrin complexed palm oil, 30% palm stearine, 10%mixed soybean mono and diglycerides

D. Preparation of Alpha-Cyclodextrin Thickened Fat Using Centrifugationand Drying.

-   Ingredients:-   30.04 lbs alpha-cyclodextrin-   37.55 lbs Oil (Palm or HO Canola)-   182.76 lbs Water-   (30 gallon mix formula)

Add 182.76 lbs water to mix tank. Start stirrers (e.g. scraped surfaceand moderate shear mixer). Add 30.04 lbs alpha-cyclodextrin to mixer.Mix for 15 minutes (or until alpha-cyclodextrin is dissolved). Add 37.55lbs of oil to mixer. Mix for 15 minutes to 1 hour. Distribute 8.8 litersof the mixture evenly into the four vessels provided with a BeckmanCoulter JS 5.0 swinging bucket rotor (Beckman Coulter, Inc., Fullerton,Calif. 92835). Balance vessels and place in rotor. Centrifuge in aBeckman Coulter J-HC high capacity, centrifuge for 15 minutes at 4500rpm (6,060×g)). Harvest top layer fat (initial moisture ˜37%). Repeatuntil all of the mixture is centrifuged. Dry top layer fat to 5% or lessmoisture. Drying should be by freeze-drying or spray drying to minimizedamage to fat structure (note: drying may not be necessary if top layerfat is to be blended at a low ratio. Blend dried top-layer fat withdesired oil mix (e.g. Palm oil, Canola, Oil blend plus emulsifiers,etc.). Blending can be accomplished with a laboratory blender or othermedium to high shear mixture. When blending with Palm Oil, warm untiloil is clear and flowable. (Heating of oil or oil/emulsifier prior toblending can assist in the more rapid dispersion of the dried toplayer.) Fat can be allowed to cool to room temperature to solidify or itcan be cooled using a scraped surface heat exchanger to form the solidfat and desired crystal structure.

E. Composition of an Alpha-Cyclodextrin Thickened Fat

The following analysis is of a blend, on a weight basis, of 60%alpha-cyclodextrin complexed HO-Canola top layer fat, 38% palm oil, 2%emulsifier (soybean mono-, di-glycerols; iodine value ˜40).

Alpha-cyclodextrin   6% (w/w) Ash   0% (w/w) Calories (no fibercorrection) 828 calories/100 grams Carbohydrates, Total 11.6% (w/w)Total Fat 86.8% (w/w) Saturated Fat 26.2% (w/w) Monounsaturated Fat45.4% (w/w) cis-cis Polyunsaturated Fat 10.8% (w/w) trans Fat 0.510%(w/w)  Moisture by Karl Fischer 1.59% (w/w) Protein by Kjeldahl (F =6.25) 0.00% (w/w)

F. Alternative Preparation of Alpha-Cyclodextrin Thickened Fat withoutCentrifugation or Drying.

-   Ingredients:-   100 kilograms Palm Oil-   3 kilograms Water-   3 kilograms alpha-cyclodextrin

Heat Palm Oil to 50° C. with constant stirring (e.g. lightning mixer at4.5 or equivalent). Bubble nitrogen gas through oil to reducesusceptibility to oxidation. In a separate vessel, mix water andalpha-cyclodextrin together so that the alpha-cyclodextrin is fullhydrated and completely suspended in the water. With a peristaltic pumpor similar transfer device slowly add alpha-cyclodextrin water mixtureto Palm Oil so that it is added slowly and evenly to completion over atwo (2) hour period. Allow Palm Oil, alpha-cyclodextrin, water mixtureto continue to stir for at least 1 hour after final addition ofalpha-cyclodextrin/water solution. Cool Palm Oil, alpha-cyclodextrin,water mixture on a water/ice bath (4° C.) with constant scraped surfacemixing.

G. Roll-in Shortening for Flaked Pastry Products

Amount Ingredient (% w/w) Dried alpha-cyclodextrin complexed Palm OilTop- 40-70  Layer Fat Palm Stearine 5-30 Palm Oil 0-15 Emulsifier(mono-, diglycerides; IV 2 to 50) 0-20

-   Alternatively,

Amount Ingredient (% w/w) Dried alpha-cyclodextrin complexed High OleicCanola 40-70  Top-Layer Fat Palm Stearine 5-30 Palm Oil 0-15 Emulsifier(mono-, diglycerides; IV 2 to 50) 0-20

In order to form the appropriate crystal structure in the roll-inshortening and the desired melting characteristics, it is necessary tovotate the above fat in a scraped surface heat exchanger.

Votation of the fat can be accomplished on a model FT25BBPA-1FC-GMargarine Crystallizer, (Armfield Inc., Jackson, N.J. 08527), consistingof two A-unit scraped surface heat exchanger barrels, one B-unitpinworker barrel, refrigerated brine for heat transfer and a progressivecavity feed pump. Typical votation parameters are listed below.

Low Preferred High Votator Parameter Value Value Value Units Feed tankoil 40 82 110 (° C.) temperature (not 104 180 230 (° F.) controlled)Feed pump speed 10 18.2 50 (%) Oil inlet temperature 30 71 90 (° C.) 86160 194 (° F.) Oil inlet pressure 1 3 15 (bar) Refrigerant inlet 4 26 40(° C.) temperature (into 39.2 79 104 (° F.) 2nd stage) Refrigerantoutlet 4 30 45 (° C.) temperature (out of 39.2 86 113 (° F.) 1st stage)A-units Scraped 200 510 800 (r.p.m.) Surface Heat Exchangers stageagitator speed A-units Scraped 1 2.75 8 (A) Surface Heat Exchangersstage drive current Interim fat 15 28 35 (° C.) temperature 59 82 95 (°F.) (1st-2nd stage) Product temperature 12 28 35 (° C.) 53.6 82 95 (°F.) B-unit Pinworker 40 500 800 (r.p.m.) agitator speed B-unit Pinworker0.5 2 8 (A) drive current Resting tube outlet 10 20 30 (° C.) fattemperature 50 68 86 (° F.)

-   The votated fat should fall within the following specifications:

Low Preferred High Measurement Value Value Value SFC at 92 degrees F. 4% 12% 20% SFC at 70 degrees F. 21% 34% 47% SFC at 50 degrees F. 35%48% 52% AOM Stability (hours) 40 80 120 Free Fatty Acids (as  0% 0.05%  0.2%  Oleic)

-   The votated fat should be tempered for optimal crystal formation.    Tempering can be accomplished by resting the fat at 15° C. to 40° C.    for one to four days. In an embodiment of the present invention, the    fat is rested at about 27° C. for two days.    H. Croissants with Roll-In Shortening-   24 Croissants-   2 sticks (0.25 lbs) roll-in shortening-   2 packages active dry yeast-   ½ cup warm water (105 to 115 F)-   ⅔ cup luke warm milk (scalded, then cooled)-   ¼ cup butter, softened-   2 tablespoons sugar-   1½ teaspoons salt-   2 eggs-   4 to 4½ cups all-purpose flour-   1 egg yolk-   1 tablespoon milk

Cut each stick shortening crosswise into 3 equal pieces. Place 2 piecesside by side on piece of waxed paper. Cover with second piece of waxedpaper. Flatten roll-in shortening into 8-inch square with rolling pin toform a solid sheet. Repeat with remaining pieces of roll-in shortening.Refrigerate squares of roll-in shortening until firm, at least 1½ hours.(Shortening must be very cold to prevent sticking when dough is rolled.)

Dissolve yeast in warm water in large bowl. Stir in ⅔ cup milk, ¼ cupbutter, the sugar, salt eggs and 2 cups of the flour. Beat until smooth.Stir in enough remaining flour to make dough easy to handle.

Turn dough onto lightly floured surface; knead until smooth and elastic,about 5 minutes. Place in greased bowl; turn greased side up. Cover; letrise in warm place until double, about 1 hour. (Dough is ready ifindentation remains when touched.) Punch down dough. Cover; refrigerate1 hour.

Punch down dough. Roll into rectangle, 25×10 inches, on lightly flouredsurface. Place 1 square firm shortening on center of dough. Fold doughover butter to make 3 layers. Turn dough one quarter turn; roll out.Repeat twice; placing shortening square on center each time. Workrapidly so shortening does not become soft. Cut dough crosswise intohalves; cover and refrigerate 1 hour.

Shape half of the dough at a time (keep other half refrigerated). Rollinto rectangle, 12×8 inches. Cut lengthwise into halves; cut each halfcrosswise into 3 squares. Cut each square diagonally into 2 triangles.Roll up each triangle, beginning at long side. Place rolls with pointsunderneath on ungreased cookie sheet; curve slightly to form crescents.Refrigerate 30 minutes.

Heat oven to 475° F. Beat egg yolk and 1 tablespoon milk slightly; brushcroissants with egg yolk mixture. Bake 5 minutes; decrease oventemperature to 400° F. Bake until croissants are brown and crisp, 8 to10 minutes.

Croissant recipe adapted from Betty Crocker's International Cookbook.Copyright © 1980 General Mills, Inc. Minneapolis, Minn. Betty Crocker'sInternational Cookbook (1980) ISBN 0-394-50453-4, p. 275.

I. Chip/Flake Shortening Fats

Amount Ingredient (% w/w) Dried alpha-cyclodextrin complexed Palm OilTop- 40-70  Layer Fat Palm Stearine 5-30 Emulsifier (mono-,diglycerides; IV 2 to 50) 0-20

-   Alternatively,

Amount Ingredient (% w/w) Dried alpha-cyclodextrin complexed High OleicCanola 40-70  Top-Layer Fat Palm Stearine 5-30 Emulsifier (mono-,diglycerides; IV 2 to 50) 0-20

-   The above fats should be melted and processed by a chipper/flaker    process unit to the following specifications.

Low Preferred High Measurement Value Value Value Thickness (inches)0.030 0.045 0.060 SFC at 10 degrees C. 24% 60% 75% SFC at 26.7 degreesC. 15% 35% 50% Hardness (Force in kg) 4 12 30 Free Fatty Acids (as  0%0.05%   0.2%  Oleic)

J. Biscuits Using Chip/Flake Shortening Fat

-   12 biscuits-   ⅓ Chip/Flake Shortening Fat-   1¾ cups all-purpose flour-   2½ teaspoons baking powder-   ¾ teaspoon salt-   ¾ cup milk

Heat oven to 450° F. Mix together refrigerated chip/flake shorteningfat, flour, baking powder and salt gently. Mix with dough mixer and addjust enough milk so dough leaves side of bowl and rounds up into a ball.(Too much milk makes dough sticky, not enough makes biscuit dry.)

Turn dough onto lightly floured surface. Knead lightly 10 times. Roll ½inch thick. Cut with floured 2-inch biscuit cutter. Place on ungreasedcookie sheet about 1 inch apart for crusty sides, touching for softsides. Bake until golden brown, 10 to 12 minutes. Immediately removefrom cookie sheet.

Biscuit recipe adapted from Betty Crocker's Cookbook New and RevisedEdition.

-   Copyright © 1978, 1969 General Mills, Inc. Minneapolis, Minn.    Library of Congress Catalog Number: 78-52003; ISBN 0-307-09823-0, p.    194.

K. Bar Filling Shortening Fat

Amount Ingredient (% w/w) Dried alpha-cyclodextrin complexed Palm OilTop- 30-70  Layer Fat Palm Stearine 5-30 Palm Oil 0-30 Emulsifier(mono-, diglycerides; IV 2 to 50) 0-20

-   Alternatively,

Amount Ingredient (% w/w) Dried alpha-cyclodextrin complexed High OleicCanola 30-70  Top-Layer Fat Palm Stearine 5-30 Palm Oil 0-30 Emulsifier(mono-, diglycerides; IV 2 to 50) 0-20

L. Bar Filling Using Alpha-Cyclodextrin Thickened Shortening Fat

-   The following filling can be used in layered bar fillings for R-T-E    cereal bars, granola bars or other variations.

Amount to Ingredient Usage Add (g) Sugar (confectionary, powder) 40.78%81.56 Flavor (Vanilla Powder) 0.32% 0.64 Salt 0.25% 0.50 NFDM (Non-fatdairy milk) 11.00% 22.00 Lecithin 0.15% 0.30 Bar Filling Shortening Fat47.50% 95.00 Total 100.00% 200.00

Warm bar filling shortening fat to 35° C. Mix sugar, vanilla powder,salt, and non-fat dairy milk together. Mix lecithin into warmed fat.Slowly add mixture of sugar, vanilla powder, salt and non-fat dairy milkto fat until fully incorporated.

M. Complexation of Palm Oil with Alpha Cyclodexdrin

Sample 1

Palm oil—940 g

AD—27 g

H₂O—33 g (a 10% excess of water was used to prevent recrystallization ofthe AD)

2IV Soy Stearine—20.4 g

Palm oil was heated to 80° C. using a jacketed beaker and stirred usinga mechanical stirrer. The AD/H₂O was added as a solution in one portionat ca. 80° C. The mixture was stirred while cooling to 50° C. andmaintained at 50° C. for 1 hour to ensure complete complexation based onresults from the slurry method. The complexation was monitored by SFCand provided similar results to those observed in the pilot plant. Afterone hour, the mixture was heated to 65° C., transferred to a small pailand allowed to solidify at ambient temperature before refrigeratingovernight.

Sample 2

Palm oil—940 g

AD—27 g

H₂O—33 g (a 10% excess of water was used to prevent recrystallization ofthe AD)

2IV Soy Stearine—20.4 g

Palm oil was heated to 80° C. using a jacketed beaker and stirred usinga mechanical stirrer. The AD/H₂O was added as a solution in one portionat ca. 80° C. The mixture was stirred while cooling to 65° C. andmaintained at 65° C. for 15 minutes. 2% 2IV soy stearine was added. Themixture was stirred an additional ten minutes at 65° C., transferred toa small pail and allowed to solidify at ambient temperature beforerefrigerating overnight.

Sample 3

Palm oil—940 g

AD—27 g

H₂O—33 g (a 10% excess of water was used to prevent recrystallization ofthe AD)

2IV Soy Stearine—20.4 g

Palm oil was heated to 50° C. using a jacketed beaker and stirred usinga mechanical stirrer. The AD/H₂O was added as a solution in one portionat ca. 80° C. The mixture was stirred at 50° C. for 1 hour. Thecomplexation was monitored by SFC as before. After one hour, the mixturewas heated to 65° C. and 2% 2IV soy stearine was added. The mixture wasstirred an additional ten minutes at 65° C., transferred to a small pailand allowed to solidify at ambient temperature before refrigeratingovernight.

Sample 4—High Shear Mixture

Palm oil—940 g

AD—27 g

H₂O—33 g (a 10% excess of water was used to prevent recrystallization ofthe AD)

2IV Soy Stearine—20.4 g

Palm oil was heated to 50° C. using a jacketed beaker and stirred usingthe high shear immersion mixer. The AD/H₂O was added as a solution inone portion at ca. 80° C. The mixture was stirred at 50° C. for 25minutes and the mixture observed by microscopy. After 25 minutes, themixture was heated to 65° C. and 2% 2IV soy stearine was added. Themixture was stirred an additional ten minutes at 65° C., transferred toa small pail and allowed to solidify at ambient temperature beforerefrigerating overnight.

Observations

Samples 1 and 3 behaved similarly, while Sample 2 separated, however,SFC and TA data for all three fats were very similar and comparable toconvectional fat useful for popcorn.

TA SFC (F and F/T) Sample 1   10-54.242 4.420 5.841 21.1-29.90326.7-19.022 33.3-12.144 37.8-7.956  Sample 2   10-53.746 5.573 8.95621.1-28.322 26.7-17.850 33.3-11.218 37.8-7.507  Sample 3   10-54.3543.369 5.152 21.1-28.338 26.7-17.758 33.3-10.793 37.8-7.613  Sample 4  10-54.288 3.776 4.600 21.1-27.797 26.7-16.920 33.3-10.185 37.8-6.456 Benchmark   10-55.552 4.291 6.028 Popcorn 21.1-25.873 Fat 26.7-16.85133.3-9.735  37.8-6.823 N. Complexation of Canola Oil with Alpha Cyclodextrin

Method 1

High oleic canola oil—750 g

10% AD/H₂O—150 g (1:1::AD;water)

2IV Soy Stearine—238 g

AMGS—119 g

High oleic canola was heated to 70° C. using a jacketed beaker andmechanical stirring. 150 g of AD/H₂O as a 1:1 mixture was heated to 80°C. at which time it became a solution. The solution was then added hotin one portion to the hot oil and the oil was allowed to cool to 15° C.When the mixture cooled to 65° C., a 70 g aliquot was taken from thebeaker and a sample of 70:20:10 was prepared. The mixture was stirred at15° C. for 1 hour and then heated to 65° C. before adding the 2IV andAMGS. The mixture was stirred for ten minutes after adding the saturatesand then poured off and hand votated before storing in the refrigeratorovernight.

Method 2

-   High oleic canola oil—500 g-   10% AD/H₂O—43.5 g (1:1::AD;water)-   2IV Soy Stearine—155.3 g-   AMGS—77.6 g

High oleic canola was cooled to 15° C. using a jacketed beaker andmechanical stirring. 43.5 g of AD/H₂O as a 1:1 mixture added slowlydropwise (0.45 g/min.) using a pump while the mixture stirred at 15° C.When the addition was complete, the mixture was stirred at 15° C. for 1hour and then heated to 65° C. before adding the 2IV and AMGS. Themixture was stirred for ten minutes after adding the saturates and thenpoured off and hand votated before storing in the refrigeratorovernight.

Method 3

-   High oleic canola oil—500 g-   10% AD/H₂O—43.5 g (1:1::AD;water)-   2IV Soy Stearine—155.3 g-   AMGS—77.6 g

High oleic canola was cooled to 70° C. using a jacketed beaker andmechanical stirring. 43.5 of AD/H₂O as a 1:1 mixture was heated to 80°C. at which time it became a solution. The solution was then added hotin one portion to the hot oil and the oil was allowed to cool to 15° C.The mixture was stirred at 15° C. for 1 hour and then heated to 65° C.before adding the 2IV and AMGS. The mixture was stirred for ten minutesafter adding the saturates and then poured off and hand votated beforestoring in the refrigerator overnight.

Method 4

-   High oleic canola oil—750 g-   10% AD/H₂O—68.3 g (1:2::AD:water)-   2IV Soy Stearine—238 g-   AMGS—119 g

High oleic canola was heated to 70° C. using a jacketed beaker andstirring. 68.3 of AD/H₂O as a 1:2 mixture was heated to 80° C. at whichtime it became a solution. The solution was then added hot in oneportion to the hot oil and the oil was allowed to cool to 15° C. Themixture was stirred at 15° C. for 1 hour and then heated to 65° C.before adding the 2IV and AMGS. The mixture was stirred for ten minutesafter adding the saturates and then poured off and hand votated beforestoring in the refrigerator overnight.

Observations Texture Analysis:

Sample Number F F/T N-1 24.174 35.631 N-2 20.731 29.470 N-3 19.14830.128 N-4 20.9011 41.960 N-5 12.9824 24.132

-   SFC:

Sample # 10° C. 21.1° C. 26.7° C. 33.3° C. 37.8° C. N-1 36.4 35.3 34.633.4 32.3 N-2 35.7 34.4 33.8 32.4 31.4 N-3 35.8 34.2 33.5 32.2 31.0 N-435.9 33.7 32.5 30.9 29.3 N-5 36.0 34.1 32.9 30.9 29.3

All patents, patent documents, and publications cited herein areincorporated by reference as if individually incorporated. Unlessotherwise indicated, all parts and percentages are by weight and allmolecular weights are weight average molecular weights. The foregoingdetailed description has been given for clarity of understanding only.No unnecessary limitations are to be understood therefrom. The inventionis not limited to the exact details shown and described, for variationsobvious to one skilled in the art will be included within the inventiondefined by the claims.

1. A fat-containing composition comprising a) a fat component havingabout 40% or less by weight of trans fat; and b) a cyclodextrin; whereinat least about 25% of the cyclodextrin in the composition is bound tothe fat.
 2. The composition of claim 1, wherein the fat component, whenat 25° C., has a viscosity less than about 12,500 cP; and thecyclodextrin is present and bound to the fat in an amount sufficient toexhibit a viscosity of a composition consisting of the fat component andthe cyclodextrin that is greater than 2 times the viscosity of the fatcomponent without the cyclodextrin.
 3. The composition of claim 1,wherein the fat component, when at 25° C., has a viscosity greater thanabout 12,500 cP; and the cyclodextrin is present and bound to the fat inan amount sufficient to exhibit a hardness of a composition consistingof the fat component and the cyclodextrin that is greater than 2 timesthe hardness of the fat component without the cyclodextrin.
 4. Thecomposition of claim 1, wherein the cyclodextrin is present and bound tothe fat in an amount sufficient to provide a composition that has aSolid Fat Content at 21.1° C. that is at least about 1% higher than theSolid Fat Content at 21.1° C. of the fat component without thecyclodextrin.
 5. The composition of claim 1, wherein the composition issubstantially free of trans-fat.
 6. The composition of claim 1, whereinthe composition comprises less than about 50% of saturated fat based ontotal fat content.
 7. The composition of claim 1, wherein least about50% of the cyclodextrin in the composition is bound to the fat.
 8. Thecomposition of claim 1, wherein the cyclodextrin is alpha-cyclodextrin.9. The composition of claim 1, wherein the fat is selected from soybeanoil, corn oil, canola oil, copra oil, cottonseed oil, safflower oil,olive oil, sunflower oil, peanut oil, palm oil, palm kernel oil, coconutoil, rice bran oil and other vegetable nut oils, butter, hydrogenatedvegetable oils and mixtures thereof.
 10. A food product comprising thecomposition of claim
 1. 11. The food product of claim 10, wherein thefood product has less than 0.5 g of trans fat per serving.